Home Vacation Home Rentals By Owner In Englewood, FL

Showing 500 Of 650 Vacation Rentals
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Exceptional(2)

$311.9

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Private Vacation Home

Heated Pool Oasis - Walk to Restaurants & Bars

Englewood, Florida, United States

Summary:brbr❤️This listing to save for later!brbrbrbrWelcome to Pineapple in Paradise a tropical getaway where old Florida charm meets modern luxury. This newly remodeled home features two private living spaces, a sparkling pool, and a fenced backyard with a bar. Perfect for families, couples, or friends to relax, unwind, and make unforgettable memories under the palms.brbrbrbr Send us a message to book your vacation.brbrbrbrThe Space:brbrFrom the moment you arrive at Pineapple in Paradise, you feel like you’ve discovered your own slice of old Florida charm wrapped in modern comfort. You’ll drop your bags, kick off your shoes, and wander out back to the sound of palm leaves and the sparkle of your private pool. The bar is stocked, the grill is ready, and the pergola calls you to unwind with a drink in hand as the sun melts into the horizon. (We can take care of stocking your fridge, just ask!)brbrbrbrYou’ll have room for everyone here, two fully equipped living spaces make it perfect for families or friends traveling together. Downstairs, you’ll find a cozy king and queen bedroom, a full kitchen, and a game-ready living room with a 75” Smart TV and PlayStation 5. brbrbrbrUpstairs, another queen bedroom and lounge space await, giving everyone a place to spread out and relax.brbrSleep comes easy on brand-new mattresses wrapped in soft linens, and mornings begin with coffee brewed in your choice of pot or Keurig before heading out to explore. brbrbrbrDearborn Street’s local cafés are just half a mile away, and Englewood and Manasota Key beaches are only minutes from your door — complete with a Boca Grande bridge pass included.brbrbrbrSpend your days paddle boarding, biking, or lounging poolside with the kids and pups, the home is both family- and pet-friendly, complete with a Pack ’n Play, high chair, and beach toys. When you’re ready to wind down, stream your favorite shows, play a few games, or gather outside under the pergola lights for one last toast to paradise.brbrbrbrAt Pineapple in Paradise, every detail is designed for connection, comfort, and that unforgettable Florida feeling , where life slows down, laughter lingers, and every moment feels like vacation. ☀️brbrbrbrGuest Access:brbrGuests have full access to the entire property including downstairs of the home, the private pool and all outdoor/backyard amenities and upstairs apartment.brbrbrbrBoat/Trailer parking is available on-site for your convenience.brbrbrbrOther Things to Note:brbrPet Fees- $35 Pet Fee - Per Pet/Per Night (No Size Limit)brbr(Capped @ $250/per pet for up to 30 days!)brbrbrbrThe fee will be requested through Airbnb after booking.
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Sleep 10

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Exceptional(7)

$306.59

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Private Vacation Home

Waterfront 3BR – Pool, Dock, Kayaks & Beach

Englewood, Florida, United States

Enjoy the best of Florida’s Gulf Coast at this newly remodeled 3-bedroom, 2-bath home with a screened-in pool, private boat dock, and plenty of parking. Just minutes to Englewood Beach and close to golf, dining, and boat-friendly hotspots, this waterfront getaway has everything you need for a relaxing, adventure-filled vacation.brbrWhy You’ll Love Itbr• Newly updated interior with open-concept layoutbr• Private boat dock on Godfrey Creek with Gulf accessbr• Just 6 minutes to Englewood Beachbr• Ample parking for cars, trailers, or boatsbrbrSleeping Arrangementsbr• Primary Bedroom: King bed, ensuite with tub/shower combobr• Guest Bedroom 1: Queen bed, large flat-screen TVbr• Guest Bedroom 2: Twin-over-full bunk bed, smart TVbr• Second full bathroom with walk-in showerbrbrOutdoor Highlightsbr• Screened lanai with private pool (heating optional)br• Outdoor dining table and separate lounging areabr• Gas grill and fire pit for evenings under the starsbr• Three kayaks and bikes ready for adventuresbr• Direct water access for boating, fishing, or kayakingbrbrInterior Comfortsbr• Large living room with flat-screen TV and board gamesbr• Sunroom with two cozy seating areas and water viewsbr• Built-in desk space for remote work or email check-insbrbrKitchen & Diningbr• Fully equipped kitchen with stainless steel appliancesbr• Granite countertops and breakfast barbr• Dining area with seating for sixbrbrIncluded Home Essentialsbr• Central A/C and fast Wi-Fibr• Full-size washer and dryerbr• Linens, towels, and starter toiletries providedbrbrNeighborhood Perksbr• 6 minutes to Englewood Beach and Stump Pass State Parkbr• Close to pickleball courts, golf courses, and boat-up diningbr• 20 minutes to Boca Grande for sandbars and world-class fishingbrbrAccess & Parkingbr• Driveway fits multiple vehicles and trailer parkingbr• Easy access to dock and boat launch areabrbrWhether you're docking your boat, relaxing poolside, or heading out to explore the coast, this spacious and stylish home is the ultimate Gulf Coast base — book now with Gulf Coast Vacations!
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$272.14

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Private Vacation Home

Dolphin Family Tides - oversized lot with privacy, walk to beach

Englewood, Florida, United States

Welcome to Dolphin Family Tides, a charming retreat nestled on almost an acre of land in the serene neighborhood of Manasota Beach, Englewood. This delightful home offers a perfect blend of comfort and convenience, making it an ideal getaway for families seeking a relaxing beach vacation.brbrDolphin Family Tides features three spacious bedrooms, including a king-sized bed in the master suite and a cozy queen-sized bed in the second bedroom, and newly renovated third family bedroom, accommodating up to 7guests comfortably. With two well-appointed bathrooms, your family will have plenty of space to unwind after a day of sun and surf.brbrThe property boasts a lovely garden view, providing a tranquil backdrop for your stay. Enjoy the pool on warm days or take advantage of the outdoor lanai for al fresco dining and relaxation. Inside, the home is equipped with modern amenities, including a fully stocked kitchen with a refrigerator, oven, microwave, and coffee maker, perfect for preparing meals together.brbrThe living area is designed for comfort, featuring a private living room with a television for entertainment. Additional amenities include air conditioning, heating, and essential safety features such as smoke and carbon monoxide detectors. For families traveling with little ones, the large yard is perfect for running and playing.brbrLocated just a short distance from the beautiful beaches of Englewood, guests can easily explore nearby attractions, including local shops, restaurants, and outdoor activities. Whether you're looking to relax by the water or embark on an adventure, Dolphin Family Tides is the perfect home base for your vacation.brbrDon't miss out on this fantastic opportunity to create lasting memories at Dolphin Family Tides. Book your stay today and experience the best of Manasota Beach!
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Sleep 7

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Exceptional(2)

$580.4

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Private Vacation Home

NEW! Palm Island with private pool, garage, screened porches, dock, 2 kayaks

Englewood, Florida, United States

brI have been an owner of VRBO properties on Palm Island for over 20 plus years. Check out my other listings for my reviews. ID # 591241, # 2831717 and ID # 1592610. This is a new member of the family. I am committed to providing the best possible experience during your stay. I will offer personal recommendation, ensure spotless accommodations and am available for any needs that arise. brbrUnwind on Palm Island at this welcoming house. With 3 bedrooms including 1 king bed and 2 queen beds, guests will feel right at home. Master suite overlooks the sunset skies on Kettle Harbor, a beautiful lagoon view. , multiple screened porches. Huge kitchen with double ovens, sub zero fridge. Salt water pool, outside shower.br Deep water dock for boats with no bridges to the Gulf and ICW. Dock has water and electric. Swim ladder at dock. Launch spot for kayaks. Pool has child safety fence, just ask and we can provide this, formal dining room, gas fireplace.brCeiling fans, garage parking for 2 cars and golf cart.brBeautiful landscaping.brbrPalm Island is ONLY accessible by car ferry or private boat. brbrPalm Island Transit runs the car ferry. Check out the website for the ferry to see current rates and ferry times.brbrThe island has a restaurant and bar.brbrWalmart, Publix and Home Dept are only a 1-3 mile drive from the mainland ferry side.brbrUnlike other Florida beaches with high rise buildings and traffic, Palm Island is seven miles of quiet, uncrowded beaches, lush wilderness and seclusion. brbrEven a short walk in the beach can feel like a treasure hunt with the bounty of shells, and shark's teeth.brbrThe fishing is world class! brbrSoak up the sun on our bath-like waters of the Gulf of Mexico, explore by kayak or stand up paddle board. We provide both free of charge.
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Exceptional(11)

$277.88

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Private Vacation Home

Family Fun-Relaxing Home w/heated Pool & Game Room

Englewood, Florida, United States

Welcome to Asbury Oasis-your favorite place for a family-FUN-cation!brbrbrJust 6.5 miles to the beach, this newly built home with a private heated pool and massive game room is the perfect place for a family vacation!brbrbrDon't feel like going to the beach Spend the day lounging in your own private pool (option to be heated - please see below in this section for more information on pool heating). Everyone will enjoy the garage space that is one giant game room. At the end of a long day in the sun, spend the evening relaxing in the screened lanai, playing board games, or catching a movie on the 75” smart TV in the living room.brbrbrThe kitchen is fully stocked with plenty of pots and pans to cook with, utensils, Keurig, drip coffee, blender, waffle maker, popcorn maker, and more! Gather around the island for snacks, laughter, and memories! brbrbrThe open living space includes a comfortable sectional couch, 2 chairs, and a 75 Roku Smart TV (we do not provide cable, but feel free to log into your favorite streaming service). All rooms have a ceiling fan.brbrbrThe master bedroom has a king size bed with French doors that step out to the pool, a large walk-in closet with plenty of storage and hangers for your personal belongings, and your own private bathroom with a standup tile/glass shower. There is also a dedicated workspace in this room along with a 43 Roku Smart TV (cable not provided).brbrbrThe 2nd bedroom (Lime Room) also has a king size bed, private closet, dresser, luggage rack, and 43 Roku Smart TV (cable not provided).brbrbrThe 3rd bedroom (Lemon Room) has a comfy daybed with a trundle, each having twin mattresses that can be used separately or combined together to make a king size bed. There is also a dresser and 43 Roku Smart TV (cable not provided). brbrbrThe 4th bedroom (Orange Room) is setup for the kiddos! It has a bunk bed with a twin over full along with a full-size trundle. This room also has bean bag chairs, a closet, dresser, a 43 Roku Smart TV (cable not provided) and a classic Nintendo console with over 600 games! Please note that the top bunk has a maximum weight capacity for 200 pounds.brbrbrThere is a 2nd full bathroom with a shower & bathtub and access to the pool area.brbrbrWasher and dryer are here for your convenience.brbrbrPool will be heated to 82 degrees. If you would like to have the pool heated above that, there will be a fee of $10 per day (fees added after booking). No partial heating will be allowed. If you would like to arrange for the pool to be heated, please let me know at least 48 hours before your scheduled check-in time. Payment must also be received at least 48 hours before your scheduled check-in time.brbrbrRenter Agreement must be signed & a picture of a Valid Driver's License uploaded at time of signing renter agreement. brbrbrDamage Security Deposit Hold of $300 required on a credit card 2 days prior to arrival.brbrbrMaximum of 8 adults, maximum of 11 total guests with combination of adults and children.brPlease note the sleeping arrangements in our home; with 8 adults, someone will be sleeping on a full-size & twin bed in the bunk room. brbrbrCheck in time is 3PM and check out time is 10AM. *There are no early check-ins or late check-outs allowed. Violations may result in monetary penalty. Our cleaning staff is on a strict schedule and early/late check-in/check-out may impeded arrival of future guests. Thank you for your cooperation!
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$184.8

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Private Vacation Home

Pelican Paradise- Pets Welcome!

Englewood, Florida, United States

Family & pet-friendly beach hub with hot tub! Enjoy a private screened deck, large yard, chef’s kitchen, and beach gear—perfect for multi-generational stays.brbr(Hot Tub Picture Coming Soon!)brbrWelcome to your spacious coastal retreat located in Englewood. This 3 bedroom, 2 bathroom home is designed to provide you with relaxed family-friendly comfort, making your beach getaway truly exceptional.brbr⭑CONTACT US FOR SEASONAL DISCOUNTS⭑brbr⭑Master Bedroom:⭑br✔ Perfect for unwinding after sun-filled beach daysbr✔ Comfortable King bed, room-darkening shades, soft & firm pillows, extra blankets, walk-in closetbr✔Private TVbrbr⭑Second Bedroom:⭑br✔ Bright and inviting oversized spacebr✔ Cozy bedding, walk-in closet, seating areabr✔Private TVbrbr⭑Third Bedroom:⭑br✔ Two comfortable swivel rocker chairs with a soft reading lamp—perfect for bedtime stories, quiet moments, or rocking little ones to sleepbr✔ A peaceful, flexible space ideal for multi-generational staysbrbr⭑Living Room:⭑br✔ Open living area featuring Italian leather seating and coastal charmbr✔ Smart TV, cozy layout for movie nightsbrbr⭑Kitchen and Dining Area:⭑br✔ Fully equipped chef’s kitchen with passthrough—perfect for staying connected while cookingbr✔ Refrigerator, oven, stove, microwave, toaster, hot water kettle, wine glassesbr✔ Dining table seats six for memorable family mealsbr✔ Coffee & wine wet bar ready for morning brews or evening poursbrbr⭑Bathrooms:⭑br✔ Two full bathrooms designed for comfort and conveniencebr✔ Shower gel, shampoo/conditioner, fresh towelsbrbr⭑Outdoor Space:⭑br✔ Hot tub tucked into the screened deck—perfect after long beach daysbr✔ Outdoor shower for rinsing off sand before hopping into the hot tubbr✔ Large yard gives kids and dogs room to run and playbr✔ Screened-in lounge patio for morning coffee br✔ Sunset viewing area—don’t forget the wine glassesbrbr⭑Additional Amenities:⭑br✔ Beach/hot tub towels, beach chairs, coolerbr✔ Life-size outdoor gamebr✔ Washer & dryer in-unitbr✔ Pet blankets provided in every closetbr✔ Single-level home—easy access throughoutbrbr⭑Safety and Security:⭑br✔ Smoke alarms installedbr✔ Private entrance for guest-only accessbrbr⭑Entertainment and Connectivity:⭑br✔ Three Smart TVsbr✔ High-speed WiFibrbr⭑Parking and Facilities:⭑br✔ Easy-access parkingbr✔ Ground-level layout for added conveniencebrbr⭑Location Highlights⭑br✔ Englewood Beach & Manasota Key (10–15 min) – White sand, shelling & Gulf sunsetsbr✔ Stump Pass Beach State Park (15 min) – Quiet nature trails & unspoiled shorelinebr✔ Lemon Bay (10 min) – Boating, kayaking mangroves & dolphin sightingsbr✔ Easy Day Trips – Venice Beach, Boca Grande, Don Pedro & Gasparilla Islands, Sarasota Aquariumbrbr⭑Services:⭑br✔ Long-term stays allowed (28+ days)br✔ Self-guided, stress-free staybrbrYour stay at Pelican Paradise promises relaxed comfort, effortless convenience, and a memorable beachside experience. Book now and start your Englewood adventure in style!brbrThe entire house is accessible, with the exception of a locked service closet by the guest bathroom. The garage in not permitted for parking, but is accessible for extra patio chairs/cushions, garbage bins and laundry.brbrWe ask that you communicate with us via the Airbnb App. We sisters will respond as quick as possible!brbrThe rear of the property abuts a low-trafficked main road. This allows for quick transportation to the beaches. While outside, there may be some noise.brbrGuests are responsible for their pet`s outdoor waste.brbr$100 Pet fee up to 2 dogsbrSMOKE-FREE Property!brbrTERMS AND CONDITIONS OF PELICAN PARADISEbrbrNO SHOW/EARLY DEPARTURE POLICYbrHosts are not responsible for Guests` inability to arrive or depart early for any reason or if members of the Guests` party do not show up. NO REFUNDS OR REBATES will be offered. Purchasing travel insurance in highly recommended.brbrREFUNDSbrYour reservation binds you to a specific period of time. Host will make every effort to correct any problem that arises during your stay in a timely manner. There should be no expectation of refund, and there will be no refund or relocation because you are disappointed with the property you have chosen to rent or in the event that something associated with the property is not working to your satisfaction. There will be no refunds or compensation for Acts of God, Mother Nature, acts of war or government agencies, road maintenance, gas shortages, power outages, or water outages. Purchasing travel insurance is highly recommended.brbrNON-SMOKING/VAPING-NO EXCEPTIONS! brThe house is SMOKE-FREE (including all patios). Guests agree to pay $350 fine.brbrDAMAGES TO PROPERTYbrPremises are to be left in clean, undamaged condition, and that Guests must follow check-in and check-out procedures. The property has been cleaned and inspected prior to Guests arrival. Guests agree to call Host immediately if damage or defects are noticed.brbrMAXIMUM OCCUPANCYbrThe maximum occupancy is 6 for any person one year old and above. Rollaway beds and inflatable mattresses are prohibited. Any unregistered guests, without the consent of the Hosts will be assessed a $50 nightly fee per person.brbrRIGHT OF ENTRYbrHosts reserve the right to enter property at anytime to investigate disturbances, check occupancy, check damages, make repairs, alterations and improvements as Hosts deem necessary.brbrMAINTENANCEbrGuests shall notify Hosts immediately of a breakdown of any property equipment, Host will try to rectify any repairs, but we can not guarantee; heat, air conditioning, electricity, water, any appliances, television, electronics, etc. No refunds or compensation will be given for failure of the above. If a repair person finds equipment was in non-working order and the problem was due to Guests oversight, neglect or misuse, Guests agree to pay the repair costs.brbrAIR CONDITIONINGbrKeep all windows and doors closed as much as possible when you have the air conditioning on. Undue stress to the air conditioning may lead to failure and repairs charged to the guest.brbrFURNITUREbrGuests agree to pay not less than $100 if furniture is rearranged.brbrCONDUCTbrOccupancy and use of premises shall not disturb or offend neighbors or residents. Quiet hours are between the hours of 9pm and 7am, as there is a Charlotte County ordinance, and you may be fined. Non-compliance can lead to cancellation and forfeiture of the reservation.brbrINSECTSbrRest assured, we do our absolute best to take care of unwanted pests. Even with regularly scheduled pest control maintenance, this is Florida, we have the occasional bug break-in. brbrPETSbr$100 pet fee per stay applies. Guests are responsible for their animals behavior and pet waste. We have onsite pet blankets in the bedroom closets to minimize damage to home items. Evidence of pet waste outside will be assessed a $20 fine per pile found.brbrHOT TUB brThe hot tub is provided as an amenity and is not guaranteed. Responsible use of the hot tub is expected. Guests understand that use of the hot tub is at their own risk. The Host shall not be liable for any injuries, illness or death resulting from the use of this amenity. brIf the hot tub requires a non-scheduled drain, deep clean, and refill due to Guest misuse (including but not limited to the addition of soaps, lotions, or food/beverages), a minimum remediation fee of $250 will be charged. Any physical damage to the hot tub shell, jets, or mechanical components will be billed at the actual professional repair cost plus a 15% administrative fee. Damage to the hot tub cover will result in an automatic replacement charge of $500.brbrPARKINGbrParking is restricted to the driveway and road only. Driving or parking on the grass is not permitted and may lead to damage to the home’s septic system. Use of the garage for parking your vehicle is prohibited.brbrSECURITY CAMERAbrFor the safety of our guests and property, there is one security camera facing the driveway.brbrThank you for taking a moment to review. We know you will take care of our house as your own!brbrThank you! Alyssa and Jocelyn
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Sleep 8

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Exceptional(62)

$187.48

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Private Vacation Home

Steps to Water! Dock, Sunsets, and Hot Tub! Englewood, Fl. The Best Kept Secret!

Englewood, Florida, United States

brListing Description:brbrWelcome to 20 Steps to Water! Dock, Sunsets, and Hot tub! brbr• Newly built dock – your gateway to the water!brbr• Gorgeous Sunsets: Enjoy stunning dock viewsbrbr• Spacious & Updated: Modern, comfortable staybrbr• Relaxing Atmosphere: Your worries melt awaybrbr• Wildlife: Watch dolphins & manatees playbrbr• Main Level Living: No steps, easy accessbrbr• Private Entry: Lower duplex unit (others live upstairs)brbr• Gourmet Kitchen: Granite countersbrbr• Outdoor Fun: Hot tub, enclosed porch, dockbrbr• Water Activities: 2 kayaks, 2 paddleboardsbrbr• Beach: 2 miles awaybrbrbrThe Space:brbr• Beautiful Location: Englewood—Less crowded, more fun!brbr• Scenic Views: Amazing water views and gorgeous sunsetsbrbr• Wildlife: Watch dolphins, manatees, and visits from Edgar the Egret or Archie the Ospreybrbr• Spacious & Updated: Completely turnkey 2 bed/1 bath, just bring your flip flops and bathing suitbrbr• Main Level Living: No steps, lower part of an up/down duplex with separate entrances and ventilationbrbr• Private & Separate: Upstairs tenant; separate entrancesbrbr• Work & Play: High-speed internet and 2 workstationsbrbr• Gourmet Kitchen: Granite counters with a view while cookingbrbr• Relaxation: Enclosed porch/lanai and hot tub for sunset viewsbrbr•Water Activities: Kayaks provided, easy to launch from the shorebrbr• Outdoor Shower: Perfect after the hot tub or water activitiesbrbr• Beach Essentials - Beach chairs , Umbrella, and Beach towels brbr• Proximity: 2 miles to Englewood Beach, 1 mile to Dearborn Stbrbr• Fishing: Great fishing from the dock or bankbrbr• Boat Friendly: Bring your boat!brbr• Comfortable Sleeping: Sleep Number king bed in the water-view bedroom, comfy queen bed in the second bedroom and Queen-size pull-out couch located in the living room.brbr• Convenience: Grab bars in the bathroom for stability, washer and dryerbrbr• Entertainment & Work: 65 Smart TV, high-speed internet, and 2 workstationsbrbr• Exclusive Amenities: Hot tub, dock, and backyard for rental guestsbrbr• Shared Laundry: Laundry area shared with upstairs tenantbrbrbrGuest Accessbrbr• Private Living Space: Your own comfortable areabrbr• Convenient Entry: Access to garage from entrywaybrbr• Garage Amenities: Washer, dryer, kayaks, paddleboard gear, and beach chairs availablebrbr• Water Equipment: 2 kayaks and 2 paddleboards located on the right side of the homebrbr• Cleaning Request: Please hose down equipment after usebrbr• Exclusive Access: Hot tub, dock, and backyard reserved for short-term rental guestsbrbr• Shared Laundry: Washer and dryer shared with upstairs tenantbrbrbrOther details to notebrbr• Self Check-In: Easy and hassle-free arrivalbrbr• Host Support: Available via phone, text, or Vrbo when neededbrbr• EV Friendly: Level 1 outlet available (adapter required)
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Exceptional(6)

$209.58

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Private Vacation Home

Treetop Cottage - super cute beach tree with great privacy and walk to beach

Englewood, Florida, United States

Welcome to Treetop Cottage, a charming retreat nestled in the heart of Englewood, just a short stroll from the beautiful Manasota Beach. This delightful two-bedroom cottage offers a cozy ambiance perfect for couples or small families looking to unwind and enjoy the coastal lifestyle.brbrTreetop Cottage features two inviting bedrooms, including a serene master suite with a comfortable queen bed, and a second bedroom that accommodates up to four guests with a queen bed and a bunk bed. The single bathroom is well-appointed, ensuring convenience for all guests.brbrStep inside to discover a warm and welcoming living area, ideal for relaxation after a day at the beach. The fully equipped kitchen boasts modern appliances, including a stove, oven, microwave, and dishwasher, making meal preparation a breeze. Enjoy your meals at the dining table or take them outside to the private patio, where you can soak up the sun or enjoy a barbecue.brbrThis cottage is designed with your comfort in mind, featuring air conditioning, heating, and essential amenities such as a washer and dryer, hairdryer, and high-speed internet. Families will appreciate the thoughtful touches, including a pack n play travel crib, high chair, and children's books and toys.brbrSafety is a priority, with smoke and carbon monoxide detectors, a fire extinguisher, and a private entrance for added peace of mind.brbrLocated in a quaint neighborhood, Treetop Cottage is just a short walk from the beach, where you can enjoy stunning sunsets and a variety of water activities. Explore nearby attractions, including local shops, restaurants, and nature trails, all within easy reach.brbrDon't miss the chance to experience the charm and comfort of Treetop Cottage. Book your stay today and create unforgettable memories by the beach!
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